NP-MRD: Showing NP-Card for 24,25-Dihydrolanosterol (NP0044545)

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Record Information

Version

2.0

Created at

2022-02-14 20:58:36 UTC

Updated at

2022-03-10 22:17:11 UTC

NP-MRD ID

NP0044545

Secondary Accession Numbers

None

Natural Product Identification

Common Name

24,25-Dihydrolanosterol

Description

24,25-Dihydrolanosterol, also known as lanostenol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, 24,25-dihydrolanosterol is considered to be a sterol lipid molecule. 24,25-Dihydrolanosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 24,25-Dihydrolanosterol is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309042000332D          

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M  END

     RDKit          3D

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M  END

  Mrv1652309042000332D          

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  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  6  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  5 13  1  1  0  0  0
  6 14  1  0  0  0  0
  8 15  1  0  0  0  0
  8 16  1  0  0  0  0
  8 17  1  1  0  0  0
 11 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 18 21  1  0  0  0  0
 18 22  1  6  0  0  0
 19 23  1  0  0  0  0
 19 24  1  0  0  0  0
 19 25  1  0  0  0  0
 21 26  1  0  0  0  0
 23 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  9 12  1  0  0  0  0
 10 15  1  0  0  0  0
 11 14  1  0  0  0  0
 20 23  1  0  0  0  0
 11 32  1  6  0  0  0
 15 33  1  6  0  0  0
 18 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0044545

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](C)(CCCC(C)C)[C@@]1([H])CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3

> <INCHI_IDENTIFIER>
InChI=1S/C30H52O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h20-22,25-26,31H,9-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1

> <INCHI_KEY>
MBZYKEVPFYHDOH-BQNIITSRSA-N

> <FORMULA>
C30H52O

> <MOLECULAR_WEIGHT>
428.7333

> <EXACT_MASS>
428.401816286

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
55.820822686353566

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol

> <ALOGPS_LOGP>
7.98

> <JCHEM_LOGP>
8.112252002333333

> <ALOGPS_LOGS>
-6.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.553786825962863

> <JCHEM_PKA_STRONGEST_BASIC>
-0.806973642323843

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
133.6947

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.52e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -0.503  -1.319   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.765  -0.517   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.843  -0.561   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.503  -2.842   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.794   0.969   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.432  -0.525   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.882  -1.967   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.148  -1.326   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.851   0.954   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.822  -3.614   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.113   1.749   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.517   1.727   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.692   2.536   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.446   0.984   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.169  -2.798   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.474  -0.575   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.264   0.663   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.106   3.337   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.459  -3.636   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.763  -1.268   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.475   4.131   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.736   4.117   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.785  -2.871   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.603  -5.355   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.833  -5.100   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.853   3.345   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -7.155  -3.672   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.222   4.146   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.600   3.359   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.969   4.160   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.607   1.778   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0       3.694   1.749   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.075  -4.153   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.099   5.326   0.000  0.00  0.00           H+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6    7                                             
CONECT    3    1    8    9                                                  
CONECT    4    1   10                                                       
CONECT    5    2   11   12   13                                             
CONECT    6    2   14                                                       
CONECT    7    2                                                            
CONECT    8    3   15   16   17                                             
CONECT    9    3   12                                                       
CONECT   10    4   15                                                       
CONECT   11    5   18   14   32                                             
CONECT   12    5    9                                                       
CONECT   13    5                                                            
CONECT   14    6   11                                                       
CONECT   15    8   19   10   33                                             
CONECT   16    8   20                                                       
CONECT   17    8                                                            
CONECT   18   11   21   22   34                                             
CONECT   19   15   23   24   25                                             
CONECT   20   16   23                                                       
CONECT   21   18   26                                                       
CONECT   22   18                                                            
CONECT   23   19   27   20                                                  
CONECT   24   19                                                            
CONECT   25   19                                                            
CONECT   26   21   28                                                       
CONECT   27   23                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   11                                                            
CONECT   33   15                                                            
CONECT   34   18                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
Lanostenol	ChEBI
(3beta,20S)-Isomer OF lanostenol	HMDB
(3beta,5XI,14xi)-isomer OF lanostenol	HMDB
5 alpha-Lanost-8-en-3 beta-ol	HMDB

Chemical Formula

C₃₀H₅₂O

Average Mass

428.7333 Da

Monoisotopic Mass

428.40182 Da

IUPAC Name

(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol

Traditional Name

(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol

CAS Registry Number

79-62-9

SMILES

[H][C@@](C)(CCCC(C)C)[C@@]1([H])CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3

InChI Identifier

InChI=1S/C30H52O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h20-22,25-26,31H,9-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1

InChI Key

MBZYKEVPFYHDOH-BQNIITSRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cannabis sativa	CannabisDB	Not Available
Chlorella vulgaris	LOTUS Database	35616633
Euphorbia kansui	LOTUS Database	35616633
Euphorbia sapinii	LOTUS Database	35616633
Fomes annosus	Fungi	KNApSAcK
Fomes fomentarius	Fungi	KNApSAcK
Fomes pini	Fungi	KNApSAcK
Saccharomyces cerevisiae	Fungi	KNApSAcK
Solanum melongena	LOTUS Database	35616633
Tillandsia recurvata	LOTUS Database	35616633
Vigna unguiculata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
14-alpha-methylsteroid
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-sterol (CHEBI:28113 )
tetracyclic triterpenoid (CHEBI:28113 )
Cholesterol and derivatives (C05109 )
Cholesterol and derivatives (LMST01010087 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	7.98	ALOGPS
logP	8.11	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	19.55	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	133.69 m³·mol⁻¹	ChemAxon
Polarizability	55.82 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0006839

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440560

PDB ID

Not Available

ChEBI ID

28113

Good Scents ID

Not Available

References

General References

Itoh T, Jeong TM, Hirano Y, Tamura T, Matsumoto T: Occurrence of lanosterol and lanostenol in seeds of red pepper (Capsicum annuum). Steroids. 1977 May;29(5):569-77. doi: 10.1016/0039-128x(77)90011-3. [PubMed:898228 ]

Showing NP-Card for 24,25-Dihydrolanosterol (NP0044545)

MOL for NP0044545 (24,25-Dihydrolanosterol)

3D MOL for NP0044545 (24,25-Dihydrolanosterol)

3D SDF for NP0044545 (24,25-Dihydrolanosterol)

3D-SDF for NP0044545 (24,25-Dihydrolanosterol)

PDB for NP0044545 (24,25-Dihydrolanosterol)

3D PDB for NP0044545 (24,25-Dihydrolanosterol)

SMILES for NP0044545 (24,25-Dihydrolanosterol)

INCHI for NP0044545 (24,25-Dihydrolanosterol)

Structure for NP0044545 (24,25-Dihydrolanosterol)

3D Structure for NP0044545 (24,25-Dihydrolanosterol)